Синтез, властивості та біологічна активність ефірів та амідів 2-оксоіндолінкарбонових кислот: Автореф. дис… канд. фармац. наук / С.В. Ковальова, Укр

Oe?a?inueea oa?iaoeaaoe/ia aeaaeaiiy

eiaaeueiaa Na?oeaia Aieiaeeie??aia

OAeE  547.756:54.04:54.057

Ceioac, aeanoeaino? oa a?ieia?/ia aeoeai?noue ao???a oa ai?ae?a 2-ieni-

?iaeie?iea?aiiiaeo eeneio

15.00.02 — oa?iaoeaaoe/ia o?i?y ? oa?iaeiaiic?y

AAOI?AOA?AO

aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy

eaiaeeaeaoa oa?iaoeaaoe/ieo iaoe

Oa?e?a — 1999

Aeena?oaoe??th ? ?oeiien.

?iaioa aeeiiaia ia eaoaae?? oieneeieia?/ii? o?i?? Oe?a?inueei?
oa?iaoeaaoe/ii? aeaaeai??, I?i?noa?noai ioi?iie caei?ia’y Oe?a?ie.

Iaoeiaee ea??aiee: aeieoi? o?i?/ieo iaoe, i?ioani?

AIEIOIA Aaea??e Aaneeueiae/

Oe?a?inueea oa?iaoeaaoe/ia aeaaeai?y, caa?aeoth/ee eaoaae?ith
aiae?oe/ii? o?i??

Io?oe?ei? iiiiaioe: aeieoi? o?i?/ieo iaoe, i?ioani?

OE?A?IAOeUe ?ai? Aaneeueiae/

Iaoe?iiaeueia oa?iaoeaaoe/ia aeaaeai?y Oe?a?ie,

i?ioani?
eaoaae?e oa?iaoeaaoe/ii? o?i??

aeieoi? oa?iaoeaaoe/ieo iaoe, i?ioani?

IAOTHI?I Aaiaae?e Iaaeiae/

Oa?e?anueeee ?inoeooo oaeineiiaeaiiy e?ea??a,

caa?aeoth/ee eaoaae?ith ee?i?/ii? a?io?i?? ?

noaeiai- iaaee/ii? oieneeieia??

I?ia?aeia onoaiiaa: Aea?aeaaiee iaoeiaee oeaio? e?ea?nueeeo cania?a

(i. Oa?e?a), eaai?aoi??y aeiiii?aeieo o?i?ei- oa?iaoeaaoe/ieo
?a/iaei oa e?iainieiieo iaoa??ae?a

Caoeno a?aeaoaeaoueny “ 1”_aeiaoiy 1999 ?ieo i 1300 aiae. ia can?aeaii?
niaoe?ae?ciaaii? a/aii? ?aaee Ae 64.605.01 i?e Oe?a?inuee?e
oa?iaoeaaoe/i?e aeaaeai?? ca aae?anith: 310002, i. Oa?e?a, aoe.
Iooe?inueea, 53.

C aeena?oaoe??th iiaeia iciaeiieoeny a a?ae?ioaoe? Oe?a?inueei?
oa?iaoeaaoe/ii? aeaaeai?? (310168, i. Oa?e?a, aoe. Aethoa?a, 4).

Aaoi?aoa?ao ?ic?neaiee “ 27 ” na?iiy 1999 ?.

A/aiee nae?aoa?

niaoe?ae?ciaaii? a/aii? ?aaee
A?EOeAIEI ?.N.

CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE

Aeooaeuei?noue oaie. Noai?aiiy iiaeo aenieiaoaeoeaieo e?ea?nueeeo
i?aia?ao?a c iecueeith oiene/i?noth ? iaei??th c iniiaieo caaea/
oa?iaoeaaoe/ii? o?i??.

O iaoiaeieia?/iiio a?aeiioaii? aeey ae??oaiiy oe??? caaea/? iae/ano?oa
aeei?enoiaothoue iaoiae iiaeeo?eaoe?? no?oeoo?e niieoe c a?aeiiith
oa?iaeieia?/iith aeoeai?noth.

Cia/iee ?ioa?an aeey iiooeo niieoe c aenieith oa?iaeieia?/iith
aeoeai?noth yaeythoue iio?aei? ?iaeieo, na?aae yeeo a?aeii? ai?iieeneioe
(o?eioioai), iae?iai?iii na?ioii?i, ?yae i?e?iaeieo aeeaei?ae?a ?
neioaoe/ieo cania?a (?iaeiiaoaoeei, aeeiaea?a?i) oa ?i. O o?i?/iiio oa
oa?iaeieia?/iiio a?aeiioaiiyo iaeiaea/aieie ? 2-ieni?iaeie?i-3-ea?aiiia?
eeneioe oa ?o iio?aei?, na?aae yeeo a?aeii? niieoee c i?ioei?e?iaiith,
i?ioecaiaeueiith, aiaeueaaoe/iith oa ?ioeie aeaeaie oa?iaeieia?/ii?
ae??.

Na?aae cacia/aieo niieoe iaeiaea/ai? ye o o?i?/iiio oae ? o
oa?iaeieia?/iiio a?aeiioaiiyo aaei?aeaee?eaoe ini(aieo ai?ae?a ? ao???a
2-ieni?iaeie?i-1-, 5- ? 7-ea?aiiiaeo eeneio, a oaeiae ai?aee
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio.

?acii c oei, no?oeoo?i? iniaeeaino? oeeo ?a/iaei aeicaieythoue
i?eionoeoe iayai?noue o ieo oieie?oe/ii?, i?ioei?e?iaii?,
i?ioecaiaeueii? oa aiaeueaaoe/ii? aeoeaiino?.

Iiooe niieoe c? aeacaieie aeaeaie oa?iaeieia?/ii? ae?? noaiiaeoue
cia/iee ?ioa?an.

Iacaai? a?oie niieoe ? neeaee i?aaeiao oeueiai aeine?aeaeaiiy.

Ca’ycie ?iaioe c iaoeiaeie i?ia?aiaie, ieaiaie, oaiaie. Aeena?oaoe?y
aeeiiaia ca?aeii c ieaiii iaoeiai-aeine?aeieo ?ia?o Oe?a?inueei?
oa?iaoeaaoe/ii? aeaaeai?? c i?iaeaie IIC Oe?a?ie (iiia? aea?aeaaii?
?a?no?aoe?? 0198 U 007011).

Iaoa ? caaea/? aeine?aeaeaiiy. Iaoith ?iaioe ? neioac iiaeo a?ieia?/ii
aeoeaieo niieoe o ?yae? ini(aieo ao???a ? ai?ae?a
3,3-ae?a?ee-2-ieni?iaeie?i-1-, 5- oa 7-ea?aiiiaeo eeneio, a oaeiae
ai?ae?a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio, aecia/aiiy iaea?eueo
ia?niaeoeaieo c ieo aeey iiaeaeueoiai ai?iaaaeaeaiiy ye iioaioe?eieo
e?ea?nueeeo cania?a.

Aeey aeinyaiaiiy cacia/aii? iaoe aoee iinoaaeai? oae? caaea/?:

cae?enieoe neioac eiaeiaoeeao?a ? iaoeeaaicienoeueoiiao?a
N,N-ae?aee?eai?iiaoeeiaeo ao???a ? N,N-ae?aee?eai?iiaee?eai?ae?a
3,3-ae?a?ee-2-ieni?iaeie?i-1-, 5- oa 7-ea?aiiiaeo eeneio;

?ic?iaeoe ??ci? i?aia?aoeai? iaoiaeeee neioaco ai?ae?a
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio:

oeyoii eiiaeainaoe?? 2-ieni?iaeie?i?a c ao??aie ienai?iiaeo eeneio;

oeyoii ai?iie?co ao???a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio;

aea/eoe eiiaeainaoe?th ao???a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio c
aeayeeie i?oi-cai?uaieie ai?e?iaie, no?oeoo?i? iniaeeaino? eio?eo
aeicaieythoue i?eionoeoe iiaeeea?noue aaoa?ioeeee?caoe??;

aea/eoe o?ceei-o?i?/i? aeanoeaino? iaea?aeaieo niieoe;

i?iaanoe oa?iaeieia?/iee ne?ei?ia iaea?aeaieo niieoe ? anoaiiaeoe
aeaiaioe ca’yceo i?ae ?o no?oeoo?ith oa oa?iaeieia?/iith aeoeai?noth;

a?ae?a?aoe iaea?eueo ia?niaeoeai? o?i?/i? niieoee aeey iiaeeaeaieo
oa?iaeieia?/ieo aeine?aeaeaiue.

Iaoeiaa iiaecia iaea?aeaieo ?acoeueoao?a. ?ic?iaeai? iaoiaee neioaco
/aoaa?oeiieo nieae ini(aieo ao???a oa ai?ae?a
3,3-ae?a?ee-2-ieni?iaeie?i-1-ioeoiaeo, 5- ? 7- ea?aiiiaeo eeneio.

Cai?iiiiiaaiee niin?a neioaco aoeeiaeo ao???a
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio ia iniia? 3-a?ae?acii?a ?caoeio,
eio?? ? aeo?aeieie niieoeaie a neioac? ai?ae?a
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio.

Aia?oa aea/ai? oiiae ai?iie?co aeacaieo ao???a a caeaaeiino? a?ae
i?e?iaee ai?i?a, ?ic/eiiee?a, iiey?ieo ni?aa?aeiioaiue i?ae aeo?aeieie
?a/iaeiaie oa oaiia?aoo?e.

Aea/ai? iniaeeaino? eiiaeainaoe?? cacia/aieo ao???a c aeayeeie
i?oi-cai?uaieie ai?e?iaie.

O ?acoeueoao? i?iaaaeaieo aeine?aeaeaiue iaea?aeaii aeecueei 70 niieoe,
ia iienaieo o e?oa?aoo??, no?oeoo?a eio?eo i?aeoaa?aeaeaia aeaieie
aeaiaioiiai aiae?co, ?*-, II?- ? ian-niaeo??a, a o aeayeeo aeiaaeeao –
cono??/iei neioacii.

Aea/aia oieie?oe/ia, i?ioecaiaeueia, aiaeueaaoe/ia oa i?ioei?e?iaia
aeoeai?noue iaea?aeaieo niieoe. Onoaiiaeai? aeaiaioe ca’yceo i?ae
no?oeoo?ith oa oa?iaeieia?/iith aeoeai?noth iaea?aeaieo ?a/iaei.

Na?aae aea/aieo ?a/iaei ciaeaeai? niieoee c aenieith oieie?oe/iith,
i?ioecaiaeueiith, aiaeueaaoe/iith oa i?ioei?e?iaiith aeoeai?noth.

I?aeoe/ia cia/aiiy iaea?aeaieo ?acoeueoao?a. ?ic?iaeai? iaoiaee
iaea?aeaiiy eiaeiaoeeao?a ? iaoeeaaicienoeueoiiao?a
N,N-ae?aee?eai?iiaoeeiaeo ao???a ? N,N-ae?aee?eai?iiaee?eai?ae?a
3,3-ae?a?ee-2-ieni?iaeie?i-1-, 5- oa 7-ea?aiiiaeo eeneio ? ai?ae?a
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio, ye? iiaeooue aooe aeei?enoai? aeey
iiaeaeueoiai ni?yiiaaiiai neioaco a?ieia?/ii aeoeaieo niieoe.

?ic?iaeaia iaoiaeeea iaea?aeaiiy aoeeiaeo ao???a
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio c aeeeth/aiiyi noaae?? io?eiaiiy
2-ieni?iaeie?i?a, ui cia/ii ciaioo? aeo?aoe iaoae?/iiai iao??th oa
aaniethoiiai aoaiieo, a oaeiae nei?i/o? /an, a?aeaaaeaiee ia neioac.

I?iaaaeaiee oa?iaeieia?/iee ne?ei?ia neioaciaaieo niieoe iioe?th?
iiaeaeueoee oe?eani?yiiaaiee iiooe iioaioe?eieo e?ea?nueeeo cania?a.

sse ia?niaeoeaiee i?ioeaeeooa??eiee can?a aeey iiaeaeueoeo iiaeeaeaieo
aeine?aeaeaiue cai?iiiiiaaii 4′-a?iiai?e?ae
5-a?ii-2-ieni?iaeie?i-3-ae?iene-eiai? eeneioe, aeey yeiai ?ic?iaeaii
i?iaeo oei/aniai? oa?iaeiiaeii? noaoo?.

?ic?iaeai? iaoiaee neioaco, a oaeiae ?acoeueoaoe o?ceei-o?i?/ieo ?
oa?iaeieia?/ieo aeine?aeaeaiue ai?iaaaeaeaii a iaoeiai-aeine?aeio ?iaioo
oa iaa/aeueiee i?ioean eaoaae? oa?iaoeaaoe/ii? o?i?? Caii??cueeiai
iaaee/iiai oi?aa?neoaoo oa Oe?a?inueei? oa?iaoeaaoe/ii? aeaaeai??.

Iniaenoee aianie caeiaoaa/a:

aenia?eiaioaeueia neioaoe/ia /anoeia ?iaioe, niaeo?aeuei?
aeine?aeaeaiiy, a oaeiae ?ic?iaea i?iaeoo OON aeeiiai? iniaenoi aaoi?ii;

?acoeueoaoe neioaoe/ieo, o?ceei-o?i?/ieo ? a?ieia?/ieo aeine?aeaeaiue
ia?iaeai?, nenoaiaoeciaai? oa i?iaiae?ciaai? aeena?oaioii.

Ai?iaaoe?y ?acoeueoao?a aeena?oaoe??. Iniiaiee ci?no aeena?oaoe?eii?
?iaioe aeiiia?aeaany ia iaoeiai-i?aeoe/i?e eiioa?aioe??, i?enay/ai?e
75-??//th Oe?OA “Aeinyaiaiiy no/anii? oa?iaoe?? – a iaaee/io i?aeoeeo”
(Oa?e?a, 1996); ia Oe?a?inuee?e eiioa?aioe?? “O?i?y acioai?nieo
aaoa?ioeeee?a” (Oa?e?a, 1997); ia Oe?a?inuee?e eiioa?aioe??, i?eo?i/ai?e
80-??//th AeAeO “OVIII Oe?a?inueea eiioa?aioe?y c i?aai?/ii? o?i??”
(Aei?i?iiao?ianuee, 1998); ia nan?? A?aeae?eaiiy o?i?? IAI Oe?a?ie
“Iaoeia? iniiae ?ic?iaee e?ea?nueeeo i?aia?ao?a” (Oa?e?a, 1998).

Ioae?eaoe??. Iaoa??aee aeena?oaoe?? iioae?eiaai? o 3 noaooyo, 1 iaoaio?
Oe?a?ie, 1 oacao aeiiia?aeae.

No?oeoo?a aeena?oaoe??. Aeena?oaoe?eia ?iaioa neeaaea?oueny c? anooio,
o?ueio ?icae?e?a, caaaeueieo aeniiae?a, nieneo e?oa?aoo?ieo aeaea?ae, 4
aeiaeaoe?a.

Caaaeueiee ia’?i aeena?oaoe?? neeaaea?  146 noi??iie.

?iaioa ?ethno?iaaia 57 noaiaie, 10 ?enoieaie ? 17 oaaeeoeyie.

Ia?ae?e aeei?enoaieo e?oa?aoo?ieo aeaea?ae i?noeoue 219 iaeiaioaaiue.

INIIAIEE CI?NO ?IAIOE

Neioac ? aeanoeaino? iniiaieo ao???a ? ai?ae?a 3,3-ae?a?ee-

2-ieni?iaeie?i-1-, 5- ? 7-ea?aiiiaeo eeneio

Io?eiaiiy aeo?aeieo 3,3-ae?a?ee-2-ieni?iaeie?i-1-ioeoiaeo eeneio (3)
cae?enithaaee oeyoii eiiaeainaoe?? 3,3-ae?a?ee-2-ieni?iaeie?i?a (1) ?
aoeeiaiai ao??o oei?ioeoiai? eeneioe a i?enooiino? aoeeaoo iao??th c
iiaeaeueoei eoaeiei a?ae?ie?cii ooai?aieo ao???a 2 (noaia 1):

Noaia 1

Iniiai? ao??e oa ai?aee iaea?aeoaaee a ?acoeueoao? eiiaeainaoe??
oei?aia?ae?eae?a 4 c 2-ae?aee?eai?iiaoaiieaie aai
2-ae?aee?eai?iiaoeeai?iaie a?aeiia?aeii. Io?eiai? a?ae?ioei?eaee
N,N-ae?aee?eai?iiaoeeiaeo ao???a ? N,N-ae?aee?eai?ii-aoeeai?ae?a
3,3-ae?a?ee-2-ieni?iaeie?i-1-ioeoiaeo eeneio (5) ia?aaiaeeee a iniiae,
ye? ca aeiiiiiaith iaoeeeiaeeaeo aai iaoeeiaiai ao??o
aaicienoeueoieeneioe ia?aoai?thaaee a /aoaa?oeii? aiii??a? nie?
caaaeueii? oi?ioee 6 (noaia 2).

Noaia 2

6: a R=H, R’=CH3, Ar=C6H4CH3-n, X=I, Y= C6H5SO3?; a R=H, R’=C2H5,
Ar=C6H4CH3-n, X=I, Y=I?; a R=5-NO2, R’=C2H5, Ar=C6H4CH3-n, X=I, Y=I?;

a R=5-Br, R’=C2H5, Ar=C6H5, X=I, Y=I?; ae R=5-Cl, R’=C2H5, Ar=C6H5, X=I,
Y=I?; a R=H, R’=C2H5, Ar=C6H4CH3-n, X=NH, Y=I?; ? R=H, R’=CH3,
Ar=C6H4CH3-n, X= NH, Y= C6H5SO3?

Neioac eiaeiaoeeao?a iniiaieo ao???a 3,3-aeeoai?e-2-ieni?iaeie?i-5- ?
7-ea?aiiiaeo eeneio (11a-ae) cae?enithaaee ca noaiith 3. Iieeaiiyi
ao???a 7 iaea?aeoaaee a?aeiia?aei? eeneioe 8, ye? aca?iiae??th c
oei?enoei o?ii?eii ia?aaiaeeee a oei?aia?ae?eaee 9. Inoaii?
eiiaeainoaaee c ae?aee?eai?iiaoaiieaie. I?e oeueiio ooai?thaaeenue
a?ae?ioei?eaee iniiaieo ao???a 10, eio?? ia?aaiaeeee a iniiae, a iio?i
i?aeaeaaaee eaaoa?i?caoe?? ca aeiiiiiaith iaoeeeiaeeaeo.

Noaia 3

11: iieiaeaiiy neeaaeiiao??ii? a?oie 5: a R=H, R?=CH3; a R=H, R?=C2H5;

a
R=CH2C6H5, R? =CH3

7: a R=H, R?=CH3;
ae R=H, R?=C2H5

Io?eiai? eiaeiaoeeaoe oa iaoeeaaicienoeueoiiaoe 6a-?, 11a-ae ?
e?enoae?/ieie niieoeaie a?eiai eieuei?o (6a–na?oei-aeiaoiai eieuei?o),
aeoaea iaei ?ic/eii? o aiae?.

No?oeoo?a niieoe i?aeoaa?aeaeaia ca aeiiiiiaith aeaiaioiiai aiae?co oa
?*-niaeo??a.

Ca aeaieie aeine?aeaeaiiy oieie?oe/ii? aeoeaiino? anoaiiaeaii, ui a
?yae? niieoe 6a-? iaea?eueo ae?aaeaiee aaeueioth/ee aieea ia
ae?yeuei?noue iaoee aeyaeythoue ao??e 6a-ae. Ii??aiyeueia ?aeaenoth/a
ni?iiiaei?noue ao??o 6a c a?eeai?eii (aiaeiaii ca oa?iaeieia?/iith
ae??th) na?ae/eoue, ui ca ooa?iaeai?eioth/ith ae??th a?i aeecueeee aei
inoaiiueiai ? ? oe?eaaei aeey iiaeeaeaiiai aea/aiiy.

Oieie?oe/ia aeoeai?noue eiaeiaoeeao?a 11a-ae caeaaeeoue a?ae i?e?iaee
aee?eueieo ?aaeeeae?a R?, iayaiino? cai?nieea a?ey e?eueoeaaiai aoiio
acioo, a oaeiae a?ae ?icoaooaaiiy neeaaeiiao??ii? a?oie a aiaeueiaaiiio
aaicieueiiio e?eueoe? (eiaeiaoeeaoe, ye? i?noyoue neeaaeiiao??io a?oio o
iieiaeaii? 5 i?e a?aenooiino? cai?nieea o e?eueoeaaiio aoiio acioo
oieie?oe/ii? aeoeaiino? ia aeyaeee). Ia?ai?uaiiy neeaaeiiao??ii? a?oie a
iieiaeaiiy 7 (niieoea 11ae) i?eaiaeeoue aei iiyaeaiiy ae?aaeaii?
oieie?oe/ii? aeoeaiino?. Aeacaia niieoea aeyaeeany iaeaeoeai?oith a
?yae? iio?aeieo 11a-ae.

Ca aino?ith oiene/i?noth aea/ai? iio?aei? ne?ae a?aeianoe aei
iaeioiene/ieo niieoe.

2. Neioac ? aeanoeaino? ai?ae?a 2-ieni?iaeie?i-3-ae?ieneeiaeo

eeneio

Neioac ai?ae?a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio cae?enithaaee aeaiia
oeyoaie. Ia?oee c ieo iieyaaa a eiiaeainaoe?? aoeeiaeo ao???a
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio c ai?iaie, a ae?oaee – a
eiiaeainaoe?? 2 ieni?iaeie?i?a c ao??aie ienai?iiaeo eeneio.

Iaiao?aei? aeey neioaco ai?ae?a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio
2-ieni?iaeie?ie 15 ? aoeeia? ao??e 2-ieni?iaeie?i-3-ae?ieneeiaeo
eeneio 16 aeiaoaaee c ?caoei?a 12 ca noaiaie 4 oa 5 a?aeiia?aeii.

Noaia 4

?caoeie 12 i?e eiiaeainaoe?? c a?ae?acei a?ae?aoii ooai?ththoue
a?ae?aciie ?caoei?a 13, ye? ca oiiaaie ?aaeoe?? E?aeia?a-Aieueoa /a?ac
ia?ao?aei? noaie A ? A ooai?ththoue iao???a? nie? 2-ieni?iaeie?i?a 14.
Inoaii? i?ae ae??th eeneio ia?aoai?ththoueny ia 2-ieni?iaeie?ie 15, ye?
a oiiaao neeaaeiiao??ii? eiiaeainaoe?? c ae?aoeeienaeaoii ca Eeyecaiii
ooai?ththoue aoeeia? ao??e 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio 16
(noaia 5):

Noaia 5

A?aoiaoth/e, ui noaia neioaco ao???a 16 c a?ae?acii?a 13 ia? ?noioiee
iaaeie?e (aeey neioaco 1 iiey oe?eueiaiai i?iaeoeoo iio??aii 6,2 iiey
iaoae?/iiai iao??th oa 1 e aaniethoiiai aoeeiaiai nie?oo), a oaeiae oa,
ui iaoae?/iee iao??e oa aaniethoiee aoaiie aeei?enoiaothoueny ye ia
noaae?? aeiaoaaiiy iao???aeo nieae 2-ieni?iaeie?i?a 14 ?c a?ae?acii?a 13
(noaia 4), oae ? ia noaae?? aeiaoaaiiy aoeeiaeo ao???a
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio 16 ?c 2-ieni?iaeie?i?a 15 (noaia
5), ie ni?iaoaaee aeeeth/eoe noaae?th aeae?eaiiy 2-ieni?iaeie?i?a 15 ?
i?iaiaeeoe eiiaeainaoe?th iao???aeo nieae 2-ieni?iaeie?i?a 14 c
ae?aoeeienaeaoii o ?aaeoe?eiiio na?aaeiaeu? i?ney caaa?oaiiy i?ioeano
a?aeiiaeaiiy a?ae?acii?a (noaia 4).

I?iaaaeai? aeine?aeaeaiiy aeicaieeee c?iaeoe aeniiaie i?i oa, ui oaeee
oeyo neioaco i?eaiaeeoue aei i?aeoe/ii iaeiaeiaeo aeoiae?a oe?eueiaeo
i?iaeoeo?a 16, ? aeicaiey? nei?ioeoe aeo?aoe iaoae?/iiai iao??th,
aaniethoiiai aoaiieo oa /ano.

Eiiaeainaoe??th aoeeiaeo ao???a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio c
ai?iaie iaea?aeoaaee ai?aee 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio.
Iaei??th c caaea/ aoei aea/eoe aieea ia cacia/aio ?aaeoe?th ??cieo
oaeoi??a – i?e?iaee ai?io, i?e?iaee ?ic/eiieea, iiey?ieo ni?aa?aeiioaiue
i?ae ao??aie 16 ? ai?iaie, oaiia?aoo?e.

Caaaeath/e ia oa, ui 3-aoeeeuei? iio?aei? 2-ieni?iaeie?io
oa?aeoa?ecothoueny aenieei nooiaiai aiie?caoe??, no?oeoo?o ao???a 16
iiaeia iiaeaoe o aeaeyae? eaoiiieo 16 ? aiieueieo A ? A oi?i,
noaa?e?ciaaieo aioo??oiueiiieaeoey?ieie aiaeiaaeie ca’yceaie (noaia 6):

Noaia 6

A?aeiii, ui iaaiaei? ?ic/eiieee iiaeooue ?noioii aieeaaoe ia oaooiia?i?
ia?aoai?aiiy, ?aaeoe?eio caeaoi?noue niieoe (iaoai?ci ? oaeaee?noue
?aaeoe?e, ?o iai?yiie), ui iiyniththoue aaaaoueia i?e/eiaie (aieea
ae?aeaeo?e/ii? i?iieeiino? na?aaeiaeua, a’yce?noth, aea??eiaith oa
niaoeeo?/iith nieueaaoaoe??th).

Aaaaoi ye? ?aaeoe?? i?aeaeathoueny a?ooieoe?iiaeueiiio eaoae?co.
Cie?aia, aioioa?i? ?ic/eiieee (nie?oe) ni?eythoue cae?eniaiith
aaaaoioeaio?iaeo (ioo-ioeueieo) iaoai?ci?a, ye? caaacia/othoue
neio?iii?noue ?ic?eao noa?eo ? ooai?aiiy iiaeo ca’yce?a, ui ? aea?aeiei
o aia?aaoe/iiio a?aeiioaii?.

Iaie anoaiiaeaii, ui a na?aaeiaeu? nie?o?a (iaoaiie, aoaiie, i?iiaiie)
eiiaeainaoe?y ia?aeiieo ae?oaoe/ieo ai?i?a c ao??aie 16 ia
a?aeaoaa?oueny. Oea iiaeia iiynieoe oei, ui oe? ao??e aeyaeythoue
eeneioi? aeanoeaino? oa c ae?oaoe/ieie ai?iaie ooai?ththoue nie? (noaia
7). A ?acoeueoao? ai?ie ao?a/athoue ioeeaio?euei?noue ? ?aaeoe?y ia
i?ioiaeeoue. Ooai?aiiy nieae 17 aoei i?aeoaa?aeaeaii iaie
aenia?eiaioaeueii.

Noaia 7

O?eaaea eei’yo?iiy ao??o 16 c ae?oaoe/ieie ai?iaie a iiey?ieo
ni?aa?aeiioaiiyo 1:1 ia i?eaiaeeoue aei ooai?aiiy ai?ae?a.

I?e aeei?enoaii? iiaea?eii? e?eueeino? ae?oaoe/ieo ai?i?a eei’yo?iiy a
cacia/aieo nie?oao i?eaiaeeoue aei ooai?aiiy iacia/ii? e?eueeino?
ai?ae?a 18 (noaia 8).

Noaia 8

18: R=H; R?=H;Br; R?= i-C3H7; ?si-C3H7; (C2H5)2N-(CH2)2; H3CO-(CH2)3;
H3C-(CH2)4; HO-C2H4; H3C-(CH2)3; HOOC-CH2; HOOC-(CH2)3; HOOC-(CH2)5

I?e oeueiio ia?aeaeueii i?ioiaeeoue i?ioean aeaaoeeethaaiiy ao???a 16 c
ooai?aiiyi N,N’-ae?aee?eienai?ae?a 19. No?oeoo?a inoaii?o aoea
i?aeoaa?aeaeaia cono??/iei neioacii i?e aca?iiae?? a?aeiia?aeieo ai?i?a
c ae?aoeeienaeaoii. Ne?ae a?aei?oeoe, ui ae?oaee i?ioean ?
ia?aaaaei?oei.

Oei /anii i?iaaaeaiiy aeacaii? eiiaeainaoe?? a na?aaeiaeu?
o?ao-aooeeiaiai nie?oo i?eaiaeeoue aei ooai?aiiy ai?ae?a 18 c aeoiaeii
iiiaae 80%. Oea, i/aaeaeii, iia’ycaii c? noa?e/ieie iniaeeainoyie
o?ao-aooaiieo a nieueaaoaoe?eieo yaeuao, a oaeiae eiai i?aeaeuaiith
ioeeaio?euei?noth a ii??aiyii? c aeuaiacaaieie nie?oaie. Ne?ae
a?aei?oeoe, ui i?ioean ai?aeoaaiiy ao???a ia?aeiieie ae?oaoe/ieie
ai?iaie oni?oii a?aeaoaa?oueny a na?aaeiaeu? iniiaieo ai?ioiiieo
?ic/eiiee?a: i??eaeei?, ae?ienai?, aeeiaoeeoi?iai?ae? i?e iiey?ieo
ni?aa?aeiioaiiyo ?aaaaio?a 1:1. I?e aeei?enoaii? iiaea?eii? e?eueeino?
ae?oaoe/iiai ai?io i?e iaa??aaii? ia eeiey/?e aiaeyi?e aai?
ooai?th?oueny noi?o a?aeiia?aeiiai ai?aeo 18 oa N,N’-ae?aee?eienai?aeo
19. A oie aea /an i?e i?iaaaeaii? ?aaeoe?? o na?aaeiaeu?
aeeiaoeeoi?iai?aeo i?e e?iiaoi?e oaiia?aoo?? c aeia?ei aeoiaeii
ooai?ththoueny ai?aee 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio.

I?e i?iaaaeaii? eiiaeainaoe?? ao???a 16 c ai?iieeneioaie a ?aaeoe?eia
na?aaeiaeua aeiaeaaaee aea?iiey?io e?euee?noue o?eaoeeai?io aeey
ca’ycoaaiiy ea?aieneeueii? a?oie.

?iaeoa iiaiaeyoue naaa a ?aaeoe?? ai?aeoaaiiy ao???a 16 a?iiaoe/i?
ai?ie. Oae, i?e aca?iiae?? ao???a 16 c ai?e?iaie a na?aaeiaeu? aoaiieo o
iiey?iiio ni?aa?aeiioaii? 1:1 c aenieei aeoiaeii ooai?ththoueny ai?e?aee
20 (noaia 9).

Noaia 9

20: R=H; NI3; R?=H;Br; Ar= C6I5; 4-Br-C6I4; 4-Cl-C6I4; 2,5-Cl2-C6I3;
4-F-C6I4; 3-I-C6I4; 4-I-C6I4; 4-COOH-C6I4; 3-COOH-4-OH-C6I3; 4-OH-C6I4;
4-CONI3-C6I4; 3-ONI3-C6I4; 4-ONI3-C6I4; 3-NI3-C6I4; 4-NI3-C6I4;

4-OC2I5-C6I4; 4-NO2-C6I4; 1-C10I7; 2-C10I7; 4-N(NI3)2-C6I4; C6I5-NI2;

4-COO(NI2)2N(C2I5)2-C6I4; 4-SCHF2-C6I4; 4-OCF3-C6I4; 3-SO2NH2-C6I4;
4-SO2NH2-C6I4; 4-Cl-C6I4-NI2; 2-C5I4N-NI2; 3-C5I4N-NI2; 3-C5I4N;
C6I5-NH(NI3); C6I5-(NI2)2; 1-C10I7-NH(NI2)2NH; C6I11

Oaea iiaaae?iea ai?e?i?a, i/aaeaeii, iiaea iiynithaaoenue oei, ui
a?iiaoe/i? ai?ie a ii??aiyii? c ae?oaoe/ieie, ? cia/ii neaae?oeie
iniiaaie a ?acoeueoao? aca?iiae?? iaiiae?eaii? ia?e aeaeo?ii?a aoiia
acioo c aeaeieae?ciaaieie (-i?a?oaeyie a?iiaoe/iiai yae?a. O ?acoeueoao?
ai?e?i ia iiaea ooai?eoe n?eue c? neaaeith eeneioith – aiieueiith
oi?iith ao???a 16 ? ?aaeoe?y ai?aeoaaiiy i?ioiaeeoue oni?oii.

Aee?e- ? a?eeai?aee 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio yaeythoue
niaith e?enoae?/i? ?a/iaeie aeiaoiai eieuei?o, ia?ic/eii? o aiae?,
?ic/eii? a ae?ienai?, aeeiaoeeoi?iai?ae? ? aeeiaoeenoeueoieneae?.
?ic/eie oeeo ?a/iaei o cacia/aieo ?ic/eiieeao c ?ic/eiii cae?ca (III)
oei?eaeo ooai?ththoue ?ioaineaia /i?ii-o?ieaoiaa caaa?aeaiiy, ui
iia’ycaii c aiie?caoe??th oeeo niieoe. C aiie?caoe??th iia’ycaia oaeiae
?ic/eii?noue oeeo niieoe o aiaeii-nie?oiaeo ?ic/eiao eoa?a.

Eeneioii-iniiai? ??aiiaaae a ?ic/eiao ai?ae?a oi?ioee 18 iiaeia iiaeaoe
noaiith 10.

Noaia 10

o oeeo niieoe ? eeoa iaeia nioaa 1663-1650 ni-1.

Ne?ae a?aei?oeoe, ui no?oeoo?a neioaciaaieo ai?ae?a aoea i?aeoaa?aeaeaia
oaeiae cono??/iei neioacii o ?acoeueoao? eiiaeainaoe?? ao???a
a?aeiia?aeieo ienai?iiaeo eeneio c 2-ieni?iaeie?iaie 15 ca Eeyecaiii
(noaia 11).

Oeacaia eiiaeainaoe?y aeeeeea? ?ioa?an ia o?eueee c oi/ee ci?o
i?aeoaa?aeaeaiiy no?oeoo?e ai?ae?a 18, i?ioa ia? oaeiae naiino?eia
cia/aiiy aeey neioaco oeeo ?a/iaei. sse i?aaeei, oeae iaoiae aeicaiey?
neioacoaaoe ai?aee c aeoiaeii ia iaioa 70%. E??i oiai, a ?yae? aeiaaee?a
neioac oe?eueiaeo i?iaeoeo?a aaea?oueny cae?enieoe eeoa ca aeiiiiiaith
inoaiiueiai iaoiaeo.

Ne?ae a?aei?oeoe, ui aoeeia? ao??e 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio
ia anooiathoue a eiiaeainaoe?th c a?eeai?iaie, eio?? i?noyoue cai?nieee
a iieiaeaii? 2 aaicieueiiai yae?a c i?e/eie noa?e/ieo ia?aoeiae aai
cai?nieee c neeueii aeyaeaieie aeaeo?iiiaeoeaioi?ieie aeanoeainoyie a
iieiaeaii? 4. Oeacai? ai?aee aaeaeiny iaea?aeaoe o?eueee ca ae?oaei
iaoiaeii.

Noaia 11

18: R=H; R?=H; NO2; R?= 2-COOH-C6I4; 3-COOH-C6I4; 2-NO2-C6I4;
2,4-Cl2-C6I3; 2-C6I5-C6I4; 4-Br-C6I4; 4-F-C6I4

Ne?ae cacia/eoe oe?eaao iiaaae?ieo aoeeiaeo ao???a
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio a ?aaeoe?? eiiaeainaoe?? c aeayeeie
i?oi-cai?uaieie ai?e?io (i-ai?iioaiie, i-oai?eaiae?ai?i). Iiaeii
i?eionoeoe, ui aeacai? ia?aoai?aiiy i?ioiaeyoue ca noaiith 12.

Noaia 12

I/aaeaeii, ia ia?o?e noaae?? oeacai? a?eeai?ie ?aaaothoue c ooai?aiiyi
i?ii?aeieo a?eeai?ae?a, eio?? aeae? i?aeaeathoueny
aioo??oiueiiieaeoey?i?e oeeee?caoe?? a ?acoeueoao? aca?iiae??
aeaeo?io?eueiiai oa ioeeaio?eueiiai oeaio??a.

No?oeoo?a iaea?aeaieo niieoe i?aeoaa?aeaeaia ca aeiiiiiaith II?-, a
oaeiae ian-niaeo?ineii??.

Ii??aiyiiy II?-niaeo?a
3-(2-ieni-2,3-aeea?ae?i-1I-?iaeie-3-?e?aeai)-1,2,3,4-oao?aa?ae?io?iienae
?i-2-iio (21a) c? niaeo?ii i?iaeoeoo eiiaeainaoe?? c i-ai?iioaiieii
na?ae/eoue i?i oa, ui aiie iiae?ai? ca iieiaeaiiyi ? ioeueoeieaoi?noth
neaiae?a, ca aeeeth/aiiyi neaiaeo i?e 11,91 i./. o niieoee 21a, eio?ee
coiiaeaiee neaiaeii i?ioiio a?oie NI o iieiaeaii? 4 o?iienae?iiaiai
oeeeeo. A?aoiaoth/e ui oeae oaeo iiaea aooe i?aeoaa?aeaeaiiyi
iaeiioeiiino? oiiieia?? no?oeoo?, ye? ii??aiththoueny, niieooe? 21a
ne?ae i?eienaoe no?oeoo?o
2-(2-ieni-2,3-aeea?ae?i-1I-?iaeie-3-?e?aeai)-3,4-aeea?ae?i-2I-1,4-aaicie
nacei-3-iio.

Neioaciaai? iaie aee?e- 18 oa a?eeai?aee 20
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio aoee i?aeaeai? oa?iaeieia?/iiio
ne?ei?iao ia aeyaeaiiy i?ioecaiaeueii?, aiaeueaaoe/ii? oa i?ioei?e?iaii?
aeoeaiino?.

sse aeyaeeinue ?yae niieoe i?iyaeythoue aenieo aioeaenoaeaoeaio
aeoeai?noue ? a a?eueoino? aeiaaee?a aeinoia??ii ia?aaeuothoue i?aia?ao
ii??aiyiiy (?iaeiiaoaoeei) a 1,4-1,8 ?ac?a. Ne?ae a?aei?oeoe, ui
iaea?eueo aeniea i?ioecaiaeueia aeoeai?noue niinoa??aa?oueny o ?a/iaei,
ye? i?noyoue o a?eeai?aeiiio caeeoeo aaeiaaie (Br, Cl), i?o?i- oa
ea?aieneeueio a?oio. I?e /iio iaeneiaeuei? cia/aiiy aeoeaiino?
niinoa??aathoueny o ieo ia ae?oao oa o?aoth aiaeeio i?ioiaeaeaiiy
caiaeueiiai i?ioeano. O ?a/iaei, ye? i?noyoue caeeoee ai?iieeneio
aeoeai?noue niinoa??aa?oueny ia 24 aiaeeio aenia?eiaioo. Aee?eai?aee ia
aeyaeee ae?aaeaii? i?ioecaiaeueii? aeoeaiino?.

I?e aeine?aeaeaii? aiaeueaaoe/ii? ae?? aoei anoaiiaeaii, ui iaea?eueo
aeoeaieie niieoeaie aeyaeeenue ai?e?aee, ye? ai?uothoue a iieiaeaii? 4
a?eeai?aeii? a?oie oae? cai?nieee, ye Br- aai NO2- a?oio. Cacia/ai?
niieoee o 1,1-1,5 ?ace ia?aaeuoaaee aiaeueaaoe/io aeoeai?noue i?aia?aoo
ii??aiyiiy (aieueoa?ai).

I?ioei?e?iaio aeoeai?noue io?eiaieo niieoe aea/aee ii a?aeiioaiith ?o
aei ne?aeoth/eo oano-ooai?a: Staphylococcus aureus (AOCC 25923),
Esherichia coli (AOCC 25922), Pseudomonas aeruginosa (AOCC 25853),
Bacillus subtilis (AOCC 6633).

Aeine?aeaeaiiy iieacaee, ui c 30 niieoe i?ioei?e?iaio aeoeai?noue o
a?aeiioaii? aei ??cieo ooai?a i?e?ii?aai?ci?a o eiioeaio?aoe??
15,62-31,25 iea/ie aeyaeee 7 niieoe, a o eiioeaio?aoe?? 62,5 iea/ie –
19. I?e oeueiio 4′-a?iiai?e?ae-5-a?ii-2-ieni?iaeie?i-3-ae?ieneeiai?
eeneioe aeyaeany aeoeaiei o a?aeiioaii? aei an?o aeei?enoaieo
oano-ooai?a.

Aiae?coth/e ?acoeueoaoe aeine?aeaeaiue iiaeia c?iaeoe aeniiaie, ui
aecia/ath/eie oaeoi?aie aeey aeyaeaiiy aea??eiai? aioei?e?iaii?
aeoeaiino? ? iayai?noue o iieiaeaii? 1 ien?iaeieueiiai e?eueoey
NI3-a?oie aai aoiio Br o iieiaeaii? 5. Iayai?noue cai?niee?a (–Br,
–NIII, –NO2, –OCH3) a a?eeai?aei?e a?oi? oaeiae aaaeeeaa aeey aeyaeaiiy
i?ioei?e?iaii? ae??. A ?yaeo aee?eai?ae?a nooo?ai ?icoe?th? niaeo? ae??
iayai?noue a iieaeoe? ?cii?ii?eueiiai caeeoeo, a oie /an, ye
ea?aieneaee?euei? caeeoee cia/iiai aieeao ia i?ioei?e?iaio aeoeai?noue
ia ni?aaeythoue.

?icoe?thth/e niaeo? i?e?ia?ieia?/ieo aeine?aeaeaiue aoei anoaiiaeaii, ui
aeey aeayeeo neioaciaaieo niieoe i?eoaiaiia i?ioeaeeooa??eia
aeoeai?noue.

I?e oeueiio iieacaii, ui
4′-a?iiai?e?ae-5-a?ii-2-ieni?iaeie?i-3-ae?iene-eiai? eeneioe ca ??aiai
aaeoa??inoaoe/ii? ? aaeoa??oeeaeii? aeoeaiino? iiaea aooe a?aeianaiee
aei ?a/iaei c iai?aaeaiith i?ioeaeeooa??eiith aeoeai?noth, yea
i?iyaey?oueny o a?aeiioaii? oieniaaiieo ooai?a ? ia i?iyaey?oueny o
a?aeiioaii? aeeooa?i?ae?a, ye? aoiaeyoue aei neeaaeo ii?iaeueii?
i?e?ioei?e iini- ? ?ioiaeioee.

Oaeei /eiii, i?iaaaeai? oa?iaeieia?/i? aeine?aeaeaiiy a?aee?eaathoue
ia?niaeoeao noai?aiiy iiaeo e?ea?nueeeo i?aia?ao?a ia iniia? iio?aeieo
2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio. Cie?aia,
4′-a?iiai?e?ae-5-a?ii-2-ieni?iaeie?i-3-ae?ieneeiai? eeneioe, yeee aeyaea
aenieo aeoeai?noue o a?aeiioaii? iaee/ee aeeooa??? i?e iecuee?e
oiene/iino? ?aeiiaiaeiaaii aeey iiaeeaeaieo oa?iaeieia?/ieo
aeine?aeaeaiue ye iioaioe?eiee i?ioeaeeooa??eiee can?a. Ia aeacaio
noanoaioe?th iaie ?ic?iaeaii i?iaeo oei/aniai? oa?iaeiiaeii? noaoo?.

CAAAEUeI? AENIIAEE

Cae?eniaii neioac eiaeiaoeeao?a oa iaoeeaaicienoeueoiiao?a
N,N-ae?aee?eai?iiaoeeiaeo ao???a oa N,N-ae?aee?eai?iiaoeeai?ae?a
3,3-ae?a?ee-2-ieni?iaeie?i-1-, 5- ? 7-ea?aiiiaeo eeneio.

Cai?iiiiiaaii niin?a neioaco ao???a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio
ia iniia? a?ae?acii?a ?caoeio, yeee aeicaiey? nei?ioeoe aeo?aoe
iaoae?/iiai iao??th, aaniethoiiai aoaiieo oa /ano, aeo?a/aiiai ia
ia?aoai?aiiy.

Oeyoii eiiaeainaoe?? aoeeiaeo ao???a 2-ieni?iaeie?i-3-ae?ieneeiaeo
eeneio c aee?e- oa a?eeai?iaie aia?oa neioaciaaii ?yae a?aeiia?aeieo
ai?ae?a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio. Aea/aii aieea ia
aeaio ?aaeoe?th ??cieo oaeoi??a (i?e?iaee ai?io, ?ic/eiieea, iiey?ieo
ni?aa?aeiioaiue i?ae aeo?aeieie ?a/iaeiaie, oaiia?aoo?e).

Aia?oa aea/aia eiiaeainaoe?y ao???a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio
c aeayeeie i?oi- cai?uaieie ai?e?io (i-oai?eaiae?ai?i, i-ai?iioaiie). A
?acoeueoao? neioaciaai?
3-(2-ieni-2,3-aeea?ae?i-1I-?iaeie-3-?e?aeai)-1,2,3,4-oao?aa?ae?io?iienae
?i-2-ii oa
2-(2-ieni-2,3-aeea?ae?i-1I-?iaeie-3-?e?aeai)-3,4-aeea?ae?i-2I-1,4-aaicie
nacei-3-ii a?aeiia?aeii.

No?oeoo?a iiaeo neioaciaaieo niieoe i?aeoaa?aeaeaia aeaieie aeaiaioiiai
aiae?co , ?*-, II?-, ian-niaeo??a, a ?yae? aeiaaee?a – cono??/iei
neioacii, a oaeiae ye?nieie ?aaeoe?yie ia ie?ai? ooieoe?iiaeuei? a?oie.
Iaoiaeii iioaioe?iiao?e/iiai oeo?oaaiiy aea/ai? eeneioii-iniiai?
aeanoeaino? ?yaeo ai?ae?a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio.

I?iaaaeaii oa?iaeieia?/iee ne?ei?ia neioaciaaieo niieoe ia oieie?oe/io,
i?ioecaiaeueio, aiaeueaaoe/io oa i?ioei?e?iaio aeoeaiino?. I?e oeueiio
aeyaeai? niieoee c aenieith oieie?oe/iith aeoeai?noth a ?yaeo
aaei?aeaee?eao?a oa iaoeeaaicienoeueoiiao?a iniiaieo ao???a ? ai?ae?a
3,3-ae?a?ee-2-ieni?iaeie?i-1-, 5- ? 7-ea?aiiiaeo eeneio ? c aenieith
i?ioecaiaeueiith, aiaeueaaoe/iith oa i?ioei?e?iaiith aeoeai?noth a ?yaeo
ai?ae?a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio.

4′-A?iiai?e?ae-5-a?ii-2-ieni?iaeie?i-3-ae?ieneeiai? eeneioe, yeee
aeyaey? aenieo i?ioeaeeooa??eio oa ae?aaeaio i?ioecaiaeueio aeoeai?noue
ia oii? iecueei? oiene/iino? a?ae?a?aiee aeey iiaeeaeaiiai
oa?iaeieia?/iiai aeine?aeaeaiiy. Ia aeacaio noanoaioe?th ?ic?iaeaii
i?iaeo oei/aniai? oa?iaeiiaeii? noaoo?.

Iaaiai?aii ieoaiiy i?i aeaiaioe ca’yceo i?ae no?oeoo?ith neioaciaaieo
niieoe oa ?o a?ieia?/iith aeoeai?noth, ui iiaea aooe aeei?enoaii aeey
iiaeaeueoiai oe?eani?yiiaaiiai iiooeo niieoe c oieie?oe/iith,
i?ioecaiaeueiith, aiaeueaaoe/iith oa i?ioei?e?iaiith aeoeaiinoyie a
?yaeo iio?aeieo 2-ieni?iaeie?iea?aiiiaeo eeneio.

Nienie iioae?eiaaieo i?aoeue ca oaiith aeena?oaoe??

Neioac, aeanoeaino? ? oieie?oe/ia aeoeai?noue eiaeiaoeeao?a
N,N-ae?aee?eai?iiaoeeiaeo ao???a 3,3-aeeoai?e-2-ieni?iaeie?i-5 oa
7-ea?aiiiaeo eeneio / A.A. Aieioia, N.A. Eiaaeueiaa, A.?. Noaiaiaiei,
N.I. Ae?iaiaic oa ?i // A?niee oa?iaoe??.– 1998.– ?1(17).– N.8-10.

Neioac, aeanoeaino? ? oieie?oe/ia aeoeai?noue eiaeiaoeeao?a oa
iaoeeaaicienoeueoiiao?a N,N-ae?aee?eai?iiaoeeiaeo ao???a oa
N,N-ae?aee?e-ai?iiaoeeai?ae?a 3,3-ae?a?ee-2-ieni?iaeie?i-1 ioeoiaeo
eeneio / A.A. Aieioia, N.A. Eiaaeueiaa, A.?. Noaiaiaiei, N.I. Ae?iaiaic
oa ?i // A?niee oa?iaoe??.– 1998.– ?1(17).– N.15-18.

Neioac, aeanoeaino? oa oa?iaeieia?/ia aeoeai?noue N-R-ai?ae?a
2-ieni-?iaeie?i-3-ae?ieneeiaeo eeneio / A.A. Aieioia, N.A. Eiaaeueiaa,
A.?. Noaiaiaiei, Ae.TH. Iaoa??iei // O?c?ieia?/ii aeoeai?
?a/iaeie.–1999.–?1(27).–N.51-54.

??oaiiy i?i aeaea/o iaoaioo Oe?a?ie ii cayaoe? ? 98105368 IIE6N07Ae
209/34, A61E 31/40. i-A?iiai?e?ae-5-a?ii-2-ieni?iaeie?i-3-ae?ieneeiai?
eeneioe, yeee i?iyaey? aioei?e?iaio aeoeai?noue o a?aeiioaii?
Corynebacterium diphtheriae / Aieioia A.A., Eiaaeueiaa N.A., Noaiaiaiei
A.?., Aeeeee ?.E. (Oe?a?ia). Cayae. 13.10.98.

Aeiaaeie aeaaoeeethaaiiy iio?aeieo 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio
/ Aieioia A.A., Noaiaiaiei A.?., Eiaaeueiaa N.A. // Oac. aeii. XVIII
Oe?a?inueei? eiioa?aioe?? c i?aai?/ii? o?i??, 6-9 aeiaoiy 1998 ?. –
Aei?i?iiao?ianuee, 1998. – N.158.

Eiaaeueiaa N.A. “Neioac, aeanoeaino? oa a?ieia?/ia aeoeai?noue ao???a oa
ai?ae?a 2-ieni?iaeie?iea?aiiiaeo eeneio”. – ?oeiien.

Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa oa?iaoeaaoe/ieo
iaoe ca niaoe?aeuei?noth 15.00.02 – oa?iaoeaaoe/ia o?i?y ?
oa?iaeiaiic?y. Oe?a?inueea oa?iaoeaaoe/ia aeaaeai?y, Oa?e?a, 1999.

Cae?eniaii neioac eiaeiaoeeao?a oa iaoeeaaicienoeueoiiao?a iniiaieo
ao???a oa ai?ae?a 3,3-ae?a?ee-2-ieni?iaeie?i-1-, 5- ? 7-ea?aiiiaeo
eeneio. Oeyoii eiiaeainaoe?? ao???a 2-ieni?iaeie?i-3-ae?ieneeiaeo eeneio
c ai?iaie, a oaeiae 2-ieni?iaeie?i?a c ao??aie ienai?iiaeo eeneio
ca Eeyecaiii cae?eniaii neioac ai?ae?a 2-ieni?iaeie?i-3-ae?ieneeiaeo
eeneio. Aea/aii aieea ia ia?oo eiiaeainaoe?th i?e?iaee ai?io, i?e?iaee
?ic/eiieea, iiey?ieo ni?aa?aeiioaiue ?aaaaio?a oa oaiia?aoo?e. No?oeoo?a
iaea?aeaieo niieoe i?aeoaa?aeaeaia aeaieie aeaiaioiiai aiae?co, ?*-,
II?- oa ian-niaeo??a. I?iaaaeaii oa?iaeieia?/iee ne?ei?ia iaea?aeaieo
niieoe. Aeey iiaeeaeaieo oa?iaeieia?/ieo aeine?aeaeaiue ?aeiiaiaeiaaii
4′-a?iiai?e?ae-5-a?ii-2-ieni?iaeie?i-3-ae?ieneeiai? eeneioe, yeee aeyaea
aenieo i?ioeaeeooa??eio oa ae?aaeaio i?ioecaiaeueio aeoeai?noue.

Eeth/ia? neiaa: 2-ieni?iaeie?i-1-, 5- oa 7-ea?aiiia? eeneioe,
2-ieni?i-aeie?i-3-ae?ieneeia? eeneioe, ao??e, ai?aee, neioac,
oa?iaeieia?/ia aeoeai?noue.

Eiaaeaaa N.A. “Neioac, naienoaa e aeieiae/aneay aeoeaiinoue yoe?ia e
aieaeia 2-ienieiaeieeiea?aiiiauo eeneio”. – ?oeiienue.

Aeenna?oaoeey ia nieneaiea o/aiie noaiaie eaiaeeaeaoa oa?iaoeaaoe/aneeo
iaoe ii niaoeeaeueiinoe 15.00.02 – oa?iaoeaaoe/aneay oeiey e
oa?iaeiaiicey. – Oe?aeineay oa?iaoeaaoe/aneay aeaaeaiey, Oa?ueeia, 1999.

Aeenna?oaoeey iinayuaia neioaco e eco/aieth oa?iaeieiae/aneie aeoeaiinoe
iaeco/aiiuo a oeie/aneii e oa?iaeieiae/aneii ioiioaieyo /aoaa?oe/iuo
nieae iniiaiuo yoe?ia e aieaeia 3,3-aeea?ee-2-ienieiaeieei-1-, 5- e 7-
ea?aiiiauo eeneio, a oaeaea aieaeia 2-ienieiaeieei-3-aeeieneeiauo
eeneio.

Iniiaiua yoe?u e aieaeu 3,3-aeea?ee-2-ienieiaeieei-1-, 5- e 7-
ea?aiiiauo eeneio iieo/aee iooai eiiaeainaoeee aaeiaaiaiaeae?eaeia
oeacaiiuo eeneio n 2-aeeaeeeeaieiiyoaiieaie e 2-aeeaeeeeaieiiyoeeaieiaie
niioaaonoaaiii. Eaaoa?iecaoeeth oeacaiiuo yoe?ia e aieaeia inouanoaeyee
n iiiiuueth eiaeenoiai iaoeea eee iaoeeiaiai yoe?a aaicienoeueoieeneiou.

Eco/aia oieieeoe/aneay aeoeaiinoue iieo/aiiuo nieae a n?aaiaiee n
a?eeaieeii. Onoaiiaeaii, /oi oieieeoe/aneay aeoeaiinoue eco/aiiuo
aauanoa caaeneo io eo no?oeoo?u. Yoe?u i?iyaeytho aieaa au?aaeaiioth
aeoeaiinoue ii n?aaiaieth n niioaaonoaothueie aieaeaie. Aeoeaiinoue a
cia/eoaeueiie noaiaie caaeneo io iieiaeaiey neiaeiiyoe?iie a?oiiu a
2-ienieiaeieeiiaii oeeeea. Iaeaieueooth aeoeaiinoue i?iyaeytho
niaaeeiaiey, o eioi?uo iia iaoiaeeony a iieiaeaiee 1 eee 7. Niaaeeiaiey,
niaea?aeauea neiaeiiyoe?ioth a?oiio a iieiaeaiee 5 iaeaaeatho
oieieeoe/aneie aeoeaiinoueth oieueei eeoue i?e iaee/ee aaiceeueiiai
?aaeeeaea o eieueoeaaiai aoiia acioa.

Aeaoiy iooyie inouanoaeai neioac aieaeia 2-ienieiaeieei-3-aeeieneeiauo
eeneio. Ia?aue ec ieo caeeth/aaony a eiiaeainaoeee yoeeiauo yoe?ia
2-ienieiaeieei-3-aeeieneeiauo eeneio n aeeoaoe/aneeie e a?iiaoe/aneeie
aieiaie. I?e yoii i?aaeeiaeai aieaa yooaeoeaiue, ii n?aaiaieth n
iienaiiui a eeoa?aoo?a, iaoiae neioaca enoiaeiuo yoeeiauo yoe?ia
2-ienieiaeieei-3-aeeieneeiauo eeneio. Iaoiae iniiaai ia
ainnoaiiaeaiee 3-aeae?aciiia ecaoeiia ii Eeaeia?o a 2-ienieiaeieeiu,
eioi?ua aac i?aaeaa?eoaeueiiai auaeaeaiey ec ?aaeoeeiiiie n?aaeu
eiiaeaine?iaaee n aeeyoeeienaeaoii ii Eeyecaio. I?aaeeiaeaiiue iaoiae
iicaieyao ia 20% nie?aoeoue ?anoiae iaoaeee/aneiai iao?ey, ia 30%
?anoiae aaniethoiiai yoaiiea, a oaeaea cia/eoaeueii oiaiueoaao a?aiy
neioaca.

Eco/aii aeeyiea ia eiiaeainaoeeth yoeeiauo yoe?ia
2-ienieiaeieei-3-aeeieneeiauo eeneio n aieiaie i?e?iaeu ?anoai?eoaey,
i?e?iaeu aieia, iiey?iuo niioiioaiee iaaeaeo yoe?ii e aieiaie, a oaeaea
oaiia?aoo?u. Onoaiiaeaii, /oi ia?ae/iua a?iiaoe/aneea aieiu anooiatho a
oeacaiioth eiiaeainaoeeth i?e eeiy/aiee a nie?oiaie n?aaea n
ia?aciaaieai niioaaonoaothueo aieeeaeia, a n aeeeeaieiaie i?e iiey?iuo
niioiioaieyo ?aaaaioia 1:1 ?aaeoeey ia eaeao. Eniieueciaaiea oaeaiaiiiai
eiee/anoaa aeeeeaieiia a yoeo oneiaeyo i?eaiaeeo a iniiaiii e
iouaieaieth yoienaeeeueiiai inoaoea o enoiaeiuo yoe?ia n ia?aciaaieai
N,N’-aeeaeeeeienaieaeia. Iaeaieaa iiaeoiaeyueie aeey yoie eiiaeainaoeee
ieacaeenue o?ao-aooeeiaue nie?o e ai?ioiiiua ?anoai?eoaee iniiaiiai
oa?aeoa?a (aeeiaoeeoi?iaieae, ie?eaeei, aeeienai). A n?aaea iineaaeieo
aeeeeaieiu oniaoii anooiatho a oeacaiioth eiiaeainaoeeth i?e iiey?iuo
niioiioaieyo enoiaeiuo i?iaeoeoia 1:1. Eniieueciaaiea oaeaiaiiiai
eiee/anoaa aeeoaoe/aneiai aieia i?e iaa?aaaiee ia eeiyuae aiaeyiie aaia
oaeaea aaaeao e ia?aciaaieth N,N’-aeeaeeeeienaieaeia. A oi aea a?aiy i?e
i?iaaaeaiee ?aaeoeee a n?aaea aeeiaoeeoi?iaieaea i?e eiiiaoiie
oaiia?aoo?a n oi?ioei auoiaeii ia?acothony aieaeu
2-ienieiaeieei-3-aeeieneeiauo eeneio. Onoaiiaeaii, /oi io?eoeaoaeueiue
enoiae ?aaeoeee a nie?oiaie n?aaea n aeeeeaieiaie naycai n
nieaia?aciaaieai iaaeaeo aieiaie e yoe?aie 2-ienieiaeieei-3-aeeieneeiauo
eeneio a aiieueiie oi?ia.

Eco/aii iiaaaeaiea enoiaeiuo yoe?ia a eiiaeainaoeee n iaeioi?uie
i?oi-caiauaiiuie aieeeiaie (i-oaieeaiaeeaiei, i-aieiioaiie).
Onoaiiaeaii, /oi a ?acoeueoaoa yoie ?aaeoeee ia?acothony
3-(2-ieni-2,3-aeeaeae?i-1I-eiaeie-3-eeeaeai)-1,2,3,4-oao?aaeae?ioeiienae
ei-2-ii e
2-(2-ieni-2,3-aeeaeae?i-1I-eiaeie-3-eeeaeai)-3,4-aeeaeae?i-2I-1,4-aaicie
nacei-3-ii niioaaonoaaiii.

No?oeoo?a aiiaue neioace?iaaiiuo niaaeeiaiee iiaeoaa?aeaeaia n iiiiuueth
yeaiaioiiai aiaeeca, EE-, II?- e iann-niaeo?ia, a a neo/aa aieaeia
2-ienieiaeieei-3-aeeieneeiauo eeneio oaeaea ano?a/iui neioacii iooai
eiiaeainaoeee 2-ienieiaeieeiia n yoe?aie ienaieiiauo eeneio ii Eeyecaio.

Iaoiaeii iioaioeeiiao?e/aneiai oeo?iaaiey a n?aaea 60% aiaeiiai
aeeienaia ii?aaeaeaiu ?Ea aieaeia 2-ienieiaeieei-3-aeeieneeiauo eeneio.

I?iaaaeai oa?iaeieiae/aneee ne?eieia aieaeia
2-ienieiaeieei-3-aeeieneeiauo eeneio ia i?ioeaiainiaeeoaeueioth,
aiaeueaaoe/aneoth e i?ioeaiiee?iaioth aeoeaiinoe. Auneacaiu niia?aaeaiey
i acaeiinayce iaaeaeo no?oeoo?ie eco/aiiuo niaaeeiaiee e eo
oa?iaeieiae/aneie aeoeaiinoueth.

Aeey oaeoaeaiiiai oa?iaeieiae/aneiai eco/aiey ioia?ai
4′-a?ii-aieeeae-5-a?ii-2-ienieiaeieei-3-aeeieneeiaie eeneiou,
i?iyaeythuee aunieoth i?ioeaiaeeooa?eeioth e au?aaeaiioth
i?ioeaiainiaeeoaeueioth aeoeaiinoe. Aeey oeacaiiiai niaaeeiaiey iieo/aii
?aoaiea i auaea/a iaoaioa Oe?aeiu e ?ac?aaioai i?iaeo a?aiaiiie
oa?iaeiiaeiie noaouee.

Eeth/aaua neiaa: 2-ienieiaeieei-1-, 5- e 7- ea?aiiiaua eeneiou,
2-ienieiaeieei-3-aeeieneeiaua eeneiou, yoe?u, aieaeu, neioac,
oa?iaeieiae/aneay aeoeaiinoue.

Kovalyova S.V. “Synthesis, properties and biological activity of esters
and amides of 2-oxoindolynecarbonic acids”. – Manuscript.

The thesis for the Master Degree of Pharmacy in Speciality 15.00.02 –
Pharmaceutical Chemistry and Pharmacognosy. – Ukrainian Academy of
Pharmacy, Kharkov, 1999.

The synthesis of iodinemethylates and methylbenzolsulfonates of
3,3-diaryl-2-oxoindolyne-1-, 5- and 7-carbonic acids basic esters and
amides has been carried out.

By means of the condensation of 2-oxoindolyne-3-glioxylic acids with
the amides as well as 2-oxoindolynes with the esters of oxomynic acids
according to Claisen method the synthesis of amides of
2-oxoindolyne-3-glyoxylic acids has been carried out.

Influence on the first condensation of amine nature, nature of the
solvent, molar ratio of reagents and temperature has been studied. The
structure of the obtained substances has been confirmed by the data of
element analysis, IR-, PMR- and mass-spectra. Pharmacological screening
of the obtained compounds has been carried out. For the profound
pharmacological studying
4′-bromanylide-5-bromine-2-oxoindolyne-3-glyoxylic acid, which has high
antidiphtherial and antiinflammatory activity has been selected.

Key words: 2-ixoindolyne-1-, 5- and 7-carbonic acids,
2-oxoindolyne-3-glyoxylic acids, esters, amides, synthesis,
pharmacological activity.

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